Can HBO Do What ABC And ESPN Failed To Do And Turn Bill Simmons Into A TV Star?

Tonight marks the first episode in a grand HBO experiment. Like Lord Varys over on HBO’s last remaining great drama Game of Thrones, the network is hoping they can raise a kingdom around an exile. And if you can appreciate that tortured analogy, you will probably really enjoy Bill Simmons’ take on sports and pop culture, which premieres on HBO tonight in Any Given Wednesday.

According to the HBO web site: “Spanning pop culture and touching on everything from sports and entertainment to arts and technology, Any Given Wednesday with Bill Simmons will feature intimate conversations with compelling guests each week. The show will also include field segments and Simmons’ signature commentary on current events.”

So this sounds like some combination of HBO’s Real Sports with the cult of personality aspects of Real Time with Bill Maher. Maher certainly seems like the template HBO is going for. Like Maher, Simmons found himself turfed by big corporate media (ESPN, specifically) and made into a martyr for ideological independence. Like Maher, Simmons is massively opinionated and resolute in his worldview. What are Simmons’ rapid-fire opinion-having promos if not his own New Rules segment?

But here’s the $18MM challenge sitting before HBO: can they make Bill Simmons a TV star? When Simmons left ESPN and Grantland, his choice to sign with HBO indicated that his television aspirations were at least as big, if not bigger, than his aspirations as a writer or publisher. The thing is, thus far, by FAR Simmons’ greatest strengths have been as a writer and publisher. As a writer, he led a one-man insurgency at ESPN, building a massive following built solely on his fan-friendly columns. As a publisher, he attracted a wildly impressive array of talent to Grantland and made that site instantly respectable and compulsively readable.

As a TV personality … not so much. Simmons’ forays into on-air roles, particularly on ESPN and ABC’s basketball coverage, were awkward to start and only got marginally better as they went along. In his writing, Simmons’ puckishness can be abrasive, but on TV it’s magnified by a factor of ten, and suddenly he’s the guy at the bar you wish you hadn’t started a conversation with. And that conversation probably ended up being about the Red Sox.

Which … isn’t necessarily a dealbreaker. Going back to Maher as a template, it’s not like HBO hasn’t been able to make abrasive personalities work before. In a sports universe that is finding itself increasingly grappling with tough questions that the owners and commissioners don’t want to have to answer for, abrasive Bill Simmons might be exactly what the doctor ordered. And you can bet that HBO, who gambled by offering him a sizable contract worth between $7MM and $9MM a year (according to The Hollywood Reporter), will do everything in their power to build awareness for their investment.

Just don’t say I didn’t warn you when he starts in on why Kanye is great or literally anything about movies.